WO2000001780A2 - Compositions de revetement en resine epoxy en phase aqueuse - Google Patents

Compositions de revetement en resine epoxy en phase aqueuse Download PDF

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Publication number
WO2000001780A2
WO2000001780A2 PCT/EP1999/004346 EP9904346W WO0001780A2 WO 2000001780 A2 WO2000001780 A2 WO 2000001780A2 EP 9904346 W EP9904346 W EP 9904346W WO 0001780 A2 WO0001780 A2 WO 0001780A2
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WO
WIPO (PCT)
Prior art keywords
epoxy
primer coating
waterbo
coating composition
epoxy resin
Prior art date
Application number
PCT/EP1999/004346
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English (en)
Other versions
WO2000001780A3 (fr
Inventor
Bastiaan Anton Van De Werff
Original Assignee
Shell Internationale Research Maatschappij B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij B.V. filed Critical Shell Internationale Research Maatschappij B.V.
Priority to AU46153/99A priority Critical patent/AU4615399A/en
Publication of WO2000001780A2 publication Critical patent/WO2000001780A2/fr
Publication of WO2000001780A3 publication Critical patent/WO2000001780A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Definitions

  • the present invention relates to waterbome epoxy resin coating compositions and in particular to waterbome epoxy resin primer compositions, to be applied on metal surfaces and in particular steel surfaces. More in particular the invention relates to waterbome epoxy resin primer compositions to be applied on metal surfaces, such as steel pipes, which are subsequently overcoated with a bitumen composition.
  • compositions were known from Newsletter, April 1998, Nr. 3 from PH0NIX, disclosing a 2 component system of emulsions of epoxy resms and of a polyfunctional epoxy curing agent (PH0NIX is a trademark) .
  • an object of the present invention was therefore, to improve said intercoat adhesion.
  • an ob ect of the present invention was to improve the intercoat adhesion between the primer coating layer and modified bitumen topcoat compositions, comprising bitumen and minor amounts of elastomers and preferably block copolymers of alkadiene such as butadiene or isoprene and monovmylarenes such as styrene .
  • the invention relates to waterbome primer coating composition
  • waterbome primer coating composition comprising
  • At least one aqueous bitumen dispersion at least one aqueous bitumen dispersion, and optionally (d) fillers, pigments, additives.
  • component (a) preferably dispersions of epoxy resins are used, wherein the epoxy resins have an epoxy equivalent weignt of at least 50C and lr particular from 500 to 2000 and more preferably from 1400 to 2000.
  • Suitable epoxy resins include reaction products of epichlorohydrm with bisphenol A or bisphenol F containing at least two oxirane rings; epoxidized novolac resins formed by a reaction of epichlorohydrm with the reaction product of phenol or alkylphenol (the alkyl having 1-10 C-atoms) and formaldehyde; reaction products of epichlorohydrm and an aliphatic polyol, such as glycerol .
  • Examples of more preferred epoxy resins to be dispersed are those of the EPON 1007 or EPIKOTE 1007 and EPON 1001 or EPIKOTE 1001 resin types (EPON and EPIKOTE are trademarks) .
  • Examples of particularly preferred dispersions to be applied are the commercially available epoxy resin dispersions EPI-REZ 3520 Y-55, EPI-REZ 5522 WY-55 and EPI-REZ 3510 W-60 (EPI-REZ is a trademark) .
  • any compound which can efficiently cure the included epoxy resin components can be applied, such as functional amine compounds, functional phenolic resins, functional anhydrides or carboxylic acids, comprising at least one functional group but preferably more functional groups.
  • the polyfunctional amme compounds which enable curing at ambient temperatures, are included in the present primer coating compositions.
  • non-polymeric polyfunctional amme having at least 2 primary or secondary ammo groups can be employed as the amme-functional curing agent m the present invention.
  • Such amines include aliphatic and cycloaliphatic amines each having 2 to 10 primary or secondary ammo groups and 2 to 100 carbon atoms.
  • Preferred non-polymeric polyfunctional amines include 2 to 4 primary ammo groups and 2 to 20 carbon atoms.
  • Suitable polyfunctional amines include, but are not limited to, hexamethylene diamine; 2-methyl pentamethyl- ene diamme; 1,3-d ⁇ ammo propane; 1,3-d ⁇ ammo pentane; dodecane diamme; 1,2-d ⁇ am ⁇ no cyclohexane; 1,4-d ⁇ ammo cyclohexane; para-phenylene diamme; 3-methyl piperidme; piperazine; N-amino ethylpiperazme; isophorone diamme; bis-hexamethylene triamme; diethylene triamme; ethylene diamme; diethylamme triamme; triethylene tetramme; tris (2-ammoethyl ) amme; ethylene oxide-amme; poly- oxyalkylene amines having from 2 to 6 oxyalkylene units and preferably from 2 to 4 oxypropylene units, such as, JEFFAMINE D, ED and T
  • the most preferred epoxy curing agent is an epoxy amme adduct such as EPICURE 8290 Y-60, which is obtainable by the reaction between an epoxy phenolic novolac and triethylene tetramine (TETA) and further reaction of the resulting amme adduct with a mono- di-, t ⁇ -glycidylether modifier and preferably monoglycidyl ether e.g. a cresyl glycidyl ether
  • curing accelerators can be used.
  • Such accelerators include: quaternary ammonium salts such as tetraethyl- ammonium chloride, tetraethylammonium bromide, cetyltri- methylammonium chloride, etc.; tertiary amines such as benzyldimethylamme, t ⁇ ethylamme, 2,4,6-(tns- dimethylammoethyl ) -phenol, etc.; amme hardening catalysts such as 2-methyl-4-methyl ⁇ m ⁇ dazole, 2-phenyl ⁇ m ⁇ dazole, l-benzyl-2-methyl ⁇ m ⁇ dazole, 2-ethyl-4-methyllmidazoleazme, lmidazoleazmes containing 11 carbon atoms (not including hexamethylene tetramine) ; lithium salts such as lithium cnlo ⁇ de, lithium bromide,
  • the fillers and/or pigments applied as component (d) can be selected from a great variety of commercially available compounds, which can provide m principle colour and barrier properties. More specifically the fillers and/or pigments can be selected from titanium dioxide, barytes, talk, calcytes, clay, kaolin, carbon black and the like, or mixtures thereof. Anti-corrosion pigments can also be included alone or in addition to other pigments and/or fillers.
  • anti-corrosion pigments can be mentioned, however without any limitation, zinc dust, zinc oxide, talc, silica dust, copper dust (especially suitable for anti- fouling pamts in marine environments, such as ship hulls and bottoms and offshore equipment), zinc phosphates, modified zinc phosphates, such as hydrates (e.g. HEUCOPHOS ZMP, ZPA, SAPP (HEUCOPHOS is a trademark) , and calcium exchange pigments e.g. SHIELDEX pigments (SHIELDEX is a trademark) .
  • Zinc phosphates or modified zinc phosphates or calcium exchange pigments are preferred.
  • the amount of pigments and fillers is in the range of from 0 to 45 vol%, relative to the total solids m the final composition .
  • Additives, wetting and dispersing additives which can stabilize tne pigments in the continuous aqueous phase, and defoammg agents, can optionally be incorporated into the present compositions, e.g. BYK 190, 154, 33.
  • the total amount of additives normally is m the range of from 0 to 10 wt% relative to the total weight of solids of component (d) .
  • bitumen dispersion can be obtained by dispersion of bitumen in the presence of a surfactant, being non- lonic, anionic or cationic, and preferably non-ionic, an amount of from 0.5 to 6% by weight, relative to the solid bitumen weight.
  • a surfactant being non- lonic, anionic or cationic, and preferably non-ionic, an amount of from 0.5 to 6% by weight, relative to the solid bitumen weight.
  • bitumen materials used m this invention include: lake asphalt such as Trinidad Epure, gilsonite, pyrobitumen, etc.; natural bitumen such as rock bitumen; cutback bitumen therefrom; petroleum bitumen and petroleum pitch such as straight asphalt and blown bitumen produced in the process of refining petroleum; cutback asphalt therefrom; mixed bitumen such as pitch bitumen, astar, etc.; flux oil, cycle oil from catalytic decomposition of heavy crude oil, cycle oil from catalytic decomposition of light crude oil, etc.
  • the lubricating oil materials used in this invention include lube cut and petroleum process oil obtained by extraction, refining and hydrogenation, etc., of the lube cut or other distillation fractions of petroleum as well as any mixture of the above.
  • bitumens having a PEN grade from 20 to 300 dmm at 25 °C.
  • PEN grade definitions and test methods are known from e.g. Shell Bitumen Industrial Handbook, 1995, London, p. 63, 64 and 100-104.
  • the penetration grade is a measurement wherein a needle of specified dimensions is allowed to penetrate into a sample of bitumen, under a known load (100 g) at a fixed temperature (25 °C) for a known time period (5 seconds). The distance over which a needle penetrates, is measured in decimillimetres (dmm) and is termed the penetration.
  • Said bitumen can if desired be modified with thermoplastic elastomers, such as butadiene-styrene block copolymers or isoprene-styrene block copolymers and preferably hydrogenated block copolymers of butadiene- styrene or isoprene-styrene (e.g. KRATON D or KRATON G block copolymers (KRATON is a trademark) ) , optionally mixed with polyolefms, an amount of from 0 to 15 wt% calculated on solid bitumen and preferably from 0 to 5% by weight.
  • thermoplastic elastomers such as butadiene-styrene block copolymers or isoprene-styrene block copolymers and preferably hydrogenated block copolymers of butadiene- styrene or isoprene-styrene (e.g. KRATON D or KRATON G block cop
  • bitumen component is incorporated into the primer - composition of the present invention, in amounts ranging from 0.5 to 50% by weight and preferably from 5 to 30% by weight, relative to the weight of the polymeric solids of the coating composition (i.e. weight of epoxy resm and curing agent) .
  • aqueous primer coating compositions as specified hereinbefore, and comprising m addition to water minor amounts of co-solvents, will also be covered by the present invention.
  • Suitable co-solvents can be selected from poly (alkylene) glycol ethers (e.g. ethylene glycol propylether or ethylene glycol monobutyl ether) , or alkanols or ketones having 1-4 carbon atoms and can be used in amounts of from 0 to 25% by weight, relative to the weight of water, and preferably from 0 to 10% by weight.
  • Flash rust inhibitors such as tertiary amines, nitrite salts and the like, can also be included as an optional additional additive in the primer coating compositions of the present invention, in an amount of from 0 to 3% by weight, relative to the total weight of solids of the coating composition (i.e. the weight of all polymeric materials, pigments, fillers) .
  • the components (a) and (b) of the coating composition of the present invention have to be stored separately until the user is ready for the actual coating processing. It will be appreciated that one of these components (a) or (b) can be included in an intermediate precomposition with other ingredients (c) and (d) .
  • the number equivalent amount of component (a) is stoichiometrically selected based on the number equivalent amount of component (b) present in the complete coating composition.
  • the stoichiometric ratio of the epoxy resin component to the functional curing agent varies in the range of from 0.8 to 2 and preferably from 1 to 1.5. Most preferably the stoichiometric ratio is from 1.1 to 1.3.
  • the cross-linking component is emulsified in water or in water and a suitable co-solvent, such as poly (alkylene) glycol ethers, (e.g. ethylene glycol propyl ether or ethylene glycol monobutyl ether) , or alkanols or ketones having 1-4 carbon atoms.
  • a suitable co-solvent such as poly (alkylene) glycol ethers, (e.g. ethylene glycol propyl ether or ethylene glycol monobutyl ether) , or alkanols or ketones having 1-4 carbon atoms.
  • the epoxy resin component in an emulsified form, containing liquid epoxy resin or epoxy resin solution is preferred. It was surprisingly found that the complete coating compositions, as specified hereinbefore, when applied as primer on metal and preferably steel surfaces, provided a significantly increased intercoat adhesion when covered with a topcoat layer of bitumen or modified bitumen enamel, e.g.
  • BITUSEAL is a trademark for a coating of bitumen, modified with styrene-butadiene block copolymer in an amount of about 9 wt% relative to the weight of the total composition. Pull off testing has been shown an increase in intercoat adhesion of 30 to 50% of the present primer compositions, depending on the modification type and intensity.
  • the coating composition is applied in general in layers of a thickness in the range from 10 to 200 microns dry film thickness, while the steel surface to be treated has a temperature in the range of from 5 to 90 °C and preferably from 5 to 45 °C.
  • the primer layer is overcoated with straight bitumen or modified bitumen at a temperature between 160 to 220 °C, using conventional equipment.
  • the coating systems are used as external coatings for in particular pipelines to protect against corrosion which if desired can be overcoated with concrete to provide negative buoyancy.
  • the coating mixture was applied to cold rolled steel panels (degreased with acetone) .
  • the mixture was allowed to cure at 40 °C in an air circulated oven. After 1 hour curing time, the panel was removed from the oven and directly overcoated with BITUSEAL of
  • EPI-REZ 5522-WY-55 14 Grams of EPI-REZ 5522-WY-55 was mixed with 1.75 grams of EPI-CURE 8290-Y-60 together with 1.25 grams of water. After stirring the coating mixture was applied to cold rolled steel panels (degreased with Acetone) . The mixture was allowed to cure at 40 °C in an air circulated oven. After 1 hour curing time, the panel was removed from the oven and directly overcoated with BITUSEAL of 190 °C and allowed to cool down. An aluminium strip with a thickness of 0.5 mm was put on top of the BITUSEAL layer. After 1 week storage at 23 °C and 50% relative humidity the panel with the coating system was cut into strips of 3.5 cm. Tne intercoat adhesion between the epoxy and BITUSEAL layer was determined by recording the required force for 90 ° pull-ofF.
  • Example 2 Instead of 200 PEN grade bitumen emulsion, as used in Example 2 a bitumen emulsion (lonically stabilized having a PEN grade of 50 at 25 °C) was added in the same weight ratios compared to Example 2. The observed intercoat adhesion was similar as in Example 1 and 2.
  • EPI-REZ 5522 WY-55 was replaced by EPI-REZ 3520 WY-55 and EPI-CURE 8290-Y-60 was replaced by EPI-CURE 8540, while similar properties were reached.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de revêtement primaire en phase aqueuse, comprenant (a) une dispersion de résine époxy en phase aqueuse, comprenant au moins une résine époxy bifonctionnelle ou polyfonctionnelle, (b) une dispersion et/ou une solution en phase aqueuse d'un durcisseur de résine époxy, (c) une dispersion de bitume en phase aqueuse, et éventuellement (d) des charges, des pigments et des additifs, le composant (b) étant de préférence un amine polyfonctionnel qui peut être appliqué pour durcir à une température ambiante. L'invention concerne également des films de revêtement primaires durcis recouvrant une surface métallique profilée.
PCT/EP1999/004346 1998-07-03 1999-06-23 Compositions de revetement en resine epoxy en phase aqueuse WO2000001780A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46153/99A AU4615399A (en) 1998-07-03 1999-06-23 Waterborne epoxy resin coating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP98202241.0 1998-07-03
EP98202241 1998-07-03

Publications (2)

Publication Number Publication Date
WO2000001780A2 true WO2000001780A2 (fr) 2000-01-13
WO2000001780A3 WO2000001780A3 (fr) 2002-05-02

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106497337A (zh) * 2016-11-18 2017-03-15 无锡明盛纺织机械有限公司 一种耐腐蚀的去甲醛水性封闭底漆
CN106497317A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用低表面处理水性环氧底漆及其制备方法
CN106497315A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用蒙脱土插层环氧树脂水性底漆及其制备方法
CN106497316A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用高性能的水性环氧富锌底漆及其制备方法
CN106497314A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用耐盐雾腐蚀性能优异的水性环氧底漆及其制备方法
CN106497318A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用具有高耐酸性能的水性环氧防腐底漆及其制备方法
EP4036175A1 (fr) * 2021-01-27 2022-08-03 Sika Technology Ag Revêtement de protection contre la corrosion à haute résistance aux chocs thermiques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112028547A (zh) * 2020-09-14 2020-12-04 郑州市路通公路建设有限公司 利用废轮胎胶粉制备的耐久型乳化沥青混合料及制备方法

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US3324041A (en) * 1964-01-17 1967-06-06 Shell Oil Co Oil-in-water settable aqueous emulsions
FR2366342A1 (fr) * 1976-10-01 1978-04-28 Exxon Research Engineering Co Composition bitumineuse et son procede de preparation
EP0695788A1 (fr) * 1994-08-05 1996-02-07 Colas S.A. Emulsion bitume/résine pour revêtement routier
EP0842982A2 (fr) * 1996-11-13 1998-05-20 Daicel Chemical Industries, Ltd. Composition durcissable, produits durcis, émulsion à base d'asphalte, liant à base d'asphalte pour chaussées et produits durcis qui en sont préparés

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106497317A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用低表面处理水性环氧底漆及其制备方法
CN106497315A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用蒙脱土插层环氧树脂水性底漆及其制备方法
CN106497316A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用高性能的水性环氧富锌底漆及其制备方法
CN106497314A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用耐盐雾腐蚀性能优异的水性环氧底漆及其制备方法
CN106497318A (zh) * 2016-10-14 2017-03-15 安徽金阳金属结构工程有限公司 一种钢结构用具有高耐酸性能的水性环氧防腐底漆及其制备方法
CN106497337A (zh) * 2016-11-18 2017-03-15 无锡明盛纺织机械有限公司 一种耐腐蚀的去甲醛水性封闭底漆
EP4036175A1 (fr) * 2021-01-27 2022-08-03 Sika Technology Ag Revêtement de protection contre la corrosion à haute résistance aux chocs thermiques
WO2022161846A1 (fr) * 2021-01-27 2022-08-04 Sherwin-Williams Coatings Deutschland Gmbh Revêtement anti-corrosion ayant une résistance élevée aux chocs thermiques

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AU4615399A (en) 2000-01-24
WO2000001780A3 (fr) 2002-05-02

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